


Kinktober 2017 Supernatural

by CrankyWhenProvoked



Category: Supernatural
Genre: Begging, Body Swap, Derogatory Language, Dirty Talk, Gun Kink, Hand Jobs, Incest Play, Kinktober 2017, Masks, Multi, Orgasm Denial, Public Hand Jobs, Rimming, Roleplay, Sleepy Sex, Teasing, Telepathic Bond, Wincest - Freeform, Worship
Language: English
Status: In-Progress
Published: 2017-10-01
Updated: 2017-10-18
Packaged: 2019-01-07 21:07:34
Rating: Mature
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 16
Words: 7,198
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/12240612
Author URL: https://archiveofourown.org/users/CrankyWhenProvoked/pseuds/CrankyWhenProvoked
Summary: This is one of my entries for the 2017 Kinktober. This one will be the Supernatural.  Each chapter will be a new day, and the warnings for that particular day will be in the notes above, plus which ship it will be. As each day goes in, the tags will update as well.The other two entries will be for Game Grumps (with Jack and Mark), and the other will be the same, but paired with the reader.





	1. Day one. Sleepy sex. Wincest

**Author's Note:**

> Day one. Sleepy sex. Wincest
> 
> Warnings: None

Sam barely registered the door of the motel opening, his senses calmed by the fact he heard the familiar rumble of the Impala before hand. It was nearly silent as Dean shuffled around, tossing off his clothes before the blankets were moved, and the bed dipped. A yawn tried to escape his lips, but was caught by Deans pressed to his, arms wrapping around his bare waist.

“Missed you.” Dean murmured against his lips, once Sam began to kiss him back.

“You too.” Sam yawned, wrapping his long arms around Deans shoulders.

Dean pressed their lips together again, drawing soft noises from Sam, his hands starting to wander, making Sams cock start to harden.

“Aren’t you tired?” Sam asked, though he didn’t try to stop his brothers movements, just let Deans hands touch him.

“I am, do you want me to stop?”

Even as he asked, his hand wrapped around the base of Sams cock, making him gasp against Deans shoulder. Shaking his head slightly, Sam wrapped his arm more secure around Dean, spreading his legs, hooking on over Deans arm. Dean took the invitation, reaching back, letting his fingers dip between Sams cheeks, circling his entrance teasingly.

“Can you reach the lube?” Dean asked, giving Sam feather light kisses.

“I can try.” Sam groaned, leaning heavily against Dean, as he reached to the nightstand.

It took a few tries, but eventually he snagged the bottle, before dropping back into his pillows, handing the bottle to Dean. Sam stretched himself out, kicking the blankets down the bed, as Dean nestled himself against his side, now slick fingers finding their way back between Sams legs. The first touch of the cold gel made Sam jolt, but as Deans warm kisses littered his neck, he relaxed again, letting Dean take care of him.

“How does that feel?” Dean teased softly, nosing just below Sams ear, as he relaxed even more into the press and tease of Deans fingers.

“Dean.” He breathed out, an answer and a sound of pleasure in one.

“That’s my baby, doing so good.” Dean praised, kissing every inch of Sams shoulder he could reach.

Sams cock twitched on his belly, his leg muscles contracting each time Dean pressed deep, making his breath catch as well.

“Can I be in you?” Dean asked, low and soft.

“Yeah.” Sam nodded, slowly.

“On your side.”

It took Sam a few moments to actually get on his side, once Dean removed his fingers, adding more lube to his own cock. Wrapping his arm under Sams head, Dean used his other hand to lift Sams leg enough to expose his hole. Sam gasped as Dean guided his cock against him, rubbing the head of his cock slowly around the rim a few times, before pressing in ever so slightly. Grasping Deans fingers, he was loose and tired as Dean worked himself into him, only stilling when they were fully pressed together.

Dean wrapped his other arm around Sams waist, pressing sleepy kisses against the crook of his neck, as he started to move. Unlike most of their times in bed lately, this one wasn’t at all rushed, Dean barely moving his hips back and forth, just enough to make both of them moan. Sam wasn’t sure how long they laid there like that, Dean moving inside him, keeping him awake enough to keep his cock hard and starting to leak.

He didn’t even react at first when Deans hand slid down his stomach, wrapping around the base of his cock, stroking it in time with the soft thrusts. Part of him almost fell asleep again, but the pressure around his cock, and the cock nudging that spot deep inside of him, felt too good to miss out on. His orgasm took him a little by surprise, body shaking as Dean stroked him through it, all nerves firing. Moments later, he felt Dean come, filling him up, his own name falling from the others lips, face pressed into his shoulder.

Sam yawned again, his body even more relaxed than before, as Dean pulled out softly, before getting up. There was once again bare recognition as Dean moved around, getting them both cleaned up before getting back into bed, molding against Sams back again.

“Good night, Sammy.” Dean whispered in his ear, getting a soft snore in response.


	2. Day two. Dirty talk. Wincest.

**Summary for the Chapter:**

> Day two. Dirty Talk. Wincest.

**Notes for the Chapter:**

> Warnings: Derogatory name calling (consensual)

“Spread um.” Dean growled lightly, holding Sams hands behind his back.

 

“Fuck you.” Sam spat, but eagerly did what Dean asked, putting on a fake struggle.

 

“You at like this every time, you little bitch. Prance that slut ass around all day, but when it’s time to actually take a dick, you act like a prude.”

 

Sam groaned in response as Dean tore his pants down his legs, leaving them to fall to his knees.

 

“Well I’m sick of it,” Dean said, tying Sams wrists in a loose knot, before grabbing the lube. “You are going to take my cock, you are going to take it up the ass like a good little bitch, and you’re going to keep your whore mouth shut, while I fill your ass with come.”

 

With another whine, Sam nodded as Deans slick fingers pressed between his cheeks, middle finger finding his hole and pressing in.

 

“I should have known,” He huffed a laugh. “That your ass would be ready for a cock already. How many dicks you let fuck you today? Three, four? Bet they all came in you too, didn’t they? Each one leaving you a little more open for the next, you begging for it the entire time.”

 

Pulling his fingers out, Dean dropped his own pants, rubbing the excess lube off his hand, over his cock before grabbing Sams hip. Holding the base of his cock, Dean lined himself up before pressing into Sam, both men groaning as each shallow thrust pressed more of him into him.

 

“Wow, those guys must have been tiny, you’re ass is still tight.”

 

Sam shifted and whined as Dean started moving, hands holding his hips still so he went at Deans pace, not his own. His cock bobbed in the air, tip shiny and damp as Dean continued to use his ass, fingers pleasure/pain dots on his skin.

 

“This ass is mine from now on, I want to know how tight you are without other guys fucking it.” Dean groaned in Sams ear, pressing them forward, Sams chest on the back of the couch.

 

Dean was more grinding into him than thrusting, but Sam was too busy moaning to try and get Dean to stop teasing him.

 

“I bet if I even touched your cock right now, it would set you off. But that wouldn’t be this fun, would it? Letting you get so close, but I’m not going to let you come, sluts like you don’t deserve it.”

 

Sam sobbed, whole body shaking, sweat dripping down his back in rivets, hands clenching at air, as Dean started thrusting again. His cock was so hard it almost was aching, as Dean continued to fuck him, hips slapping together.

 

“I think I’m going to be nice to my little whore, let you get yourself off, so I don’t have to touch it, but I want to feel you come around my dick.”

 

The moment Sams hands were free, his hand was around his cock, beating it in the same rhythm that Dean was still going, his mouth open in a silent moan. When he came, he was lucky Dean was behind him, when his knees went weak, body squeezing. With a curse, Dean was following him, filling him up, some dripping down their legs.

 

Sliding to the floor, Dean helped Sam lay down, before he laid down next to him, each trying to get their breath back.

 

“Next time,” Dean coughed, looking over at Sam. “I’m not letting you touch yourself, it’s come untouched, or not at all.”

 

Sam whined, tossing his arm over his eyes, his cock giving an interested twitch.


	3. Day Three. Public. Wincest.

**Summary for the Chapter:**

> Day Three. Public. Wincest.

**Notes for the Chapter:**

> Warnings: Uhhh public

When Dean was asked later, he would deny that he came up with a real plan, it was just a spur of the moment thing; a boring, long car ride and a sleeping brother. Sam would call bull shit, and tell him that he had a fetish for doing things in the car, and of course Dean would deny everything.

 

In reality, it was a boring long ride that gave him the opportunity to do what was in his mind, but it wasn’t the first time he thought about it. And they had talked about it before, Dean touching him awake, giving him permission to wake him up with pleasure.

 

They had just passed another mile marker, some staticy rock station on the radio, a comfortable breeze coming in through the windows. Dean was fueled by the empty coffee cups now littered around Sams feet, but Sam was fast asleep. Which Dean was fine with, seeing as the other hadn’t slept for very long the night before, before Dean was waking him and telling him there was a case. At first Sam had tried to stay up, but as soon as Dean put soft rock on the radio, he was gone.

 

So Dean let him sleep for a few hours, before the idea that was pressing down on his brain, felt like the right time to execute. Gripping the steering wheel with his left hand, he moved his right to the front of Sams pants, rubbing gently. The action made Sam shift a little, but he stayed asleep, giving Dean the courage to slowly undo his belt, before popping the button and unzipping the zipper.

 

By the time Dean fully got Sams cock out, he was already half hard, and Dean took no time to wrap his hand around the base. Sams mouth fell open a little, sleepy pleasure sounds sneaking out, as Dean started stroking him. In his own jeans, his cock was starting to pulse, the exciting fear of a car going past and seeing exactly what he was doing. Sam was still making the snuffling moans, his hips unconsciously moving, his hands gripping at the seat.

 

It was only when Dean started focusing just on the head, that Sam finally woke up, a long drawn out moan coming from his lips.

 

“Dean, what the fuck.” He gasped, head falling back against the seat.

 

“Morning, Sammy.” Dean smiled at him, before looking back at the road, hand going back to stroking him fully.

 

“Fuck, I.. Damn it.” Sam panted, trying to find it in him to be mad, but Dean knew exactly how to make him forget how to speak.

 

“Feel good?” Dean smirked, twisting his wrist at each upstroke, using Sams precome to slick the way.

 

“De.” Was the most he could get out, before he was dissolving into moans again.

 

Checking to make sure there was no one really around, Dean pulled to the side of the road, putting the car in park. Undoing his seat belt, he moved to straddle Sams legs, pressing their lips together, going back to pumping his cock. Sams moans doubled as he fought to Deans pants open, getting his cock out and starting to work him over at the same pace Dean had set.

 

“Fuck, Sammy.” Dean growled, pressing their foreheads together.

 

Sam was the first to come, streaking his shirt with come, his deep moans setting Dean off, adding to the mess. Dean all the fell back into his seat, his chest heaving up and down in the, now sticky air.

 

“I hate you some days,” Sam grumbled, taking his shirt off and tossing it in the back once he bundled it up.

 

“That’s not a nice way to talk to someone who just got you off.” Dean laughed, as he fixed his pants and pulled them back on the road.

 

“You couldn’t have waited until we stopped for the night?” He asked, pulling his own pants back up and fastened.

 

“Nope.”

 

“Jerk.”

 

“Bitch.”


	4. Day Four. Begging. Wincest

**Summary for the Chapter:**

> Day Four. Begging. Wincest

**Notes for the Chapter:**

> Wanings: Heavy teasing

The handcuffs clinked softly as they wrapped around Deans wrists, keeping him horizontal on the bed, his arms comfortably spread. Sitting between his legs, Sam had an almost evil smirk on his face, one that Dean recognized from his own facial expressions. But this time, Sam had gotten the jump on him, got in the shower first, meaning Sam was able to plan this. Which meant Dean was left to Sams mercy, and the hard throb beneath his towel, told more than his mouth did.

“Come on, Sammy. Do something.” Dean teased, squirming as Sam smacked his thigh.

“Uh uh, my pace.” He shook his head, running his fingers up and down his thighs, pressing in harder the higher he got.

“Sammy.” Dean groaned, as Sams long fingers finally got to his balls, the tips just barely brushing them.

“Hmm?”

“I know you said your pace, but come on.”

“I will eventually, not sure if it’s going to be on your face or in your ass.”

Dean groaned again, shifting on the bed as Sams fingers continued to tease his balls, with just barely there brushes. A deep groan worked its way from Deans throat as Sam moved the towel out of the way, running his fingertips now over his hard shaft.

“Fuck, that’s it, baby.” Dean moaned, but then let out a whine as Sam moved his touch away. “Come on, Sammy.”

“You’re still not getting it, De. We are going to go at my pace, even if you becoming a begging mess, I’m going at my speed.”

Dean gasped softly, before getting a glint in his eyes, Sam swallowing hard.

“Oh, you want me to beg, huh?”

“Shut up.” Sam huffed, taking his hands off Dean.

“Oh what? You going to just fuck me?” He smirked, wiggling his hips.

Sam cocked an eyebrow at him for a moment before standing up, Dean sputtered as Sam walked into the bathroom, pushing the door mostly closed.

“Oh come on, Sam. It was a joke.” Dean sighed, pulling lightly at the handcuffs.

Looking around, Dean couldn’t see anything close enough to him to grab to help him get unlocked, but found the surrounding completely empty.

“Sammy, come on. You’re not going to really leave me like this, are you?”

The only response he got was silence, not even the creak of floor tiles, the only sound coming from outside the motel.

“Sammy, please come back here and finish what you started, or let me go so I can do it myself.”

Sam let out a deep chuckle, which sent shivers down Deans spine, but there still wasn’t movement suggesting Sam was coming out. It was quiet for a little longer, before Dean noticed a slick rhythmic sound coming from the bathroom, confusing him for a moment. He didn’t get it until Sam let out a deep groan of pleasure, that it hit him, sending a jolt of arousal deep through him.

“You fucker.” Dean groaned.

The response was Sam making more noise, the slick noise getting louder, and the squirt of a lubricant bottle.

“Come on, Sammy. Fuck. Please come back, I’ll be good.”

“I dunno,” Sam panted. “My hand’s doing a pretty good job.”

“Sam, come back here, I need you to touch me.” Dean shifted, his erection back in full swing, twitching each time Sam let out another noise of pleasure. “I’m sorry, please come here and fuck me, or ride me, I don’t care.”

“Still think you’re more work than what I’m doing.”

“Sam.” Dean stifled the whine working up his throat. “I want you, please. I need to feel you, come here, please?”

Deans whole body jolted as Sam finally opened the door, walking out with his slick hand still around his cock. Biting his lip, Dean spread his legs, sure later he would tell Sam to stuff it if he asked about it, but right now he needed to be touched.

“Please, Sammy?” Dean sighed, cock twitching as Sam slowly stroked his own cock.

“Please what?”

“I don’t care, just do something to me.”

Climbing on the bed, Sam knelt between Deans knees, leaning over him to press their lips together, the backs of his knuckles brushing Deans cock. As Dean kissed him back, he did his best pressing himself against Sam, groaning deeply as Sam wrapped his hand around his cock as well. The lube was already warm and very slick, as Sam stroked them, giving a small twist of his wrist when he hit their heads.

Dean was the first to let go, covering Sams chest, his head falling back into the pillows, the long line of his neck exposed. Sam pressed kisses to the sweaty skin, digging teeth in as he followed Dean over the edge.

“You suck.” Dean huffed, as Sam grabbed the towel under Dean to clean them up.

“Nah, just good at getting what I want.” And that smirk was back, feeling an odd mix of indigence and arousal. And maybe just a little pride.


	5. Day Five. Body Swap. Wincest

**Summary for the Chapter:**

> Day five. Body Swap. Wincest

**Notes for the Chapter:**

> Warnings: None

“Son of a fuck witches.” Dean growled as him and Sam slammed into the motel room.

“I told you not to provoke them.” Sam snapped back, going to push his hair back, but only finding short locks.

“Stop messing up my hair.” Dean mumbled, taking off the jacket that the body he was in, Sams, was wearing.

“Oh, I can mess with your hair any other time, but when it’s me doing it from inside your body it’s weird.”

“No weirder than that sentence.”

Sam rolled his eyes, taking off his coat and over shirt, tossing them on the empty bed.

“We’re not going to get anywhere fighting, go shower, I’m going to call Bobby.”

“Ok.” Dean sighed, pushing at Sams hair for at least the millionth time since the incident happened.

Dean stripped the rest of his clothes off, heading into the bathroom and closing the door, as Sam started telling Bobby what was up. Looking in the mirror, it still tripped him out seeing Sams face stare back at him. When the ‘bomb’ went off, at first he hadn’t noticed what was wrong, only that he was no longer carrying the bag he had had two seconds earlier. It wasn’t until Sam swore, and it came out as Deans voice, that they both noticed.

Rubbing his face, he turned the shower on and stepped in, letting the water run over him, letting out another sigh. The water in this room didn’t last long, so Dean tried to hurry, washing Sams stupid long hair, before he started washing his body. Dean felt tripped out as he ran his hands down Sams torso, muscles so familiar but foreign to him with these hands. As he stood there, he became less interested in getting washed off, and more with touching the spots that drove Sam wild.

Cupping his balls in his hand, his body shivered, and he was quick to turn the water off and stepping out and grabbing a towel. Not even bothering with wrapping it around himself, he dried himself a little, before opening the door.

“So Bobby said,” Sam trialed off, looking over at Dean. “Wha?”

“Come here, Sammy.”

Sam was confused, but stood up and came over to Dean, feeling out of sorts having to look up at himself, but when Dean grabbed his hips, he didn’t care anymore.

“Dean?” He whined, grabbing Deans shoulders.

“You’re in my body, means I know exactly what I like and can use it to rock your world.”

Sam moaned again, running his fingers into ‘Deans hair’, giving it a tug, listening to Dean moan, his knees almost going out on him.

“You really like that, don’t you?” Dean panted, digging his nails into Sams hips, earning another moan.

“Yep, and if you get on the bed, on your knees, I can show you what else I like.”

Dean rushed to comply, getting on the bed and putting his hips up in the air, groaning at how he knows he looks. Sams hands were on his cheeks as he climbed on the bed, spreading Deans cheeks, thumbs digging in roughly. Dean thought Sam was going to ease into it, so when he went straight in, it made him jump, but soon he was moaning. Sam always knew exactly what to do with his tongue, but feeling it through Sams skin, was electrifying. There was no doubt Sam knew what he liked, and he for sure knew what he was doing, since it took no time for Dean to start begging, his cock throbbing between his legs.

Sams hand grabbing his balls was a new shock, and just made him whine, hands gripping the pillow in a death grip. When Sam finally started stroking his cock, it took no time before he was coming, whole body seizing up.

“God damnit.” Dean breathed, rolling onto his back, pulling Sam on top of him.

Kissing himself felt weird at first, but the two melted into it, as Deans hand slid into Sams pants, slowly jerking him off. Sam came with a whine, pressing his face into Deans neck, panting as Dean milked him through it. Relaxing to Deans side, Sam got his breathing back to normal, as Dean wrote nonsense with his finger tips.

“So, what did Bobby say?” Dean asked, a few minutes later.

“Huh? Oh, so get this.”


	6. Day Six. Telepathic bonds. Sabriel

**Summary for the Chapter:**

> Day Six. Telepathic bonds. Sabriel

**Notes for the Chapter:**

> Warnings: Angel powers in action

A low whine was working in Sams throat as he tried to move his arms, but they wouldn’t budge from where they were against the mattress. His legs felt the exact same, how much he wanted to move but he just couldn’t, his brain not working on telling his limbs to move. The culprit was straddling Sams thighs, in nothing but a pair of boxers, hands wrapped around Sams cock.

“Enjoying yourself?” Gabriel smirked, twisting his lube slicked hands.

Sam pressed his lips together tighter, not willing to try and talk again, seeing as what came out wasn’t what he wanted to say.

“Now come on, use your big boy words, tell me exactly what you want.”

All Gabe got was a shake of the head, his lips still pressed tightly together, swallowing as his smirk grew.

“Oh Sammy, I can make you talk.” He said, sliding up Sams body slightly, his boxers now gone.

Sams mouth popped open as the head of his cock brushed Gabes hole, warm and already very wet, and Sam would bet Gabe could just take him to the hilt without trying. Closing his mouth again, he hoped that Gabe would just get on with it, But he didn’t seem to want that just yet, first he was going to play with him.

“Sure you don’t have anything to say?” Gabe asked again, moving back and forth slowly, just the head of Sams dick pressing in and out.

It felt like there was a brace around his cock, keeping it exactly where Gabe wanted it to be, exactly where he needed it to fuck himself on. Gabe kept up the pace, moving down a little bit more each time, Sams mouth fighting to stay closed.

“Doesn’t this feel good, your cock sliding in my ass?” Gabe asked, pressing kisses around Sams tattoo, up to his neck.

Sams mouth drooped open, soft groans slipping out as Gabe got fully seated, staying still for a few moments before coming all the way to the head before going back again.

“Just say it.” Gabe purred, nipping his neck. “Just open your mouth and let it come out.”

“Please fuck me.” Sam groaned out, not caring how he sounded anymore, as Gabe made another agonizingly slow.

“What was that, couldn’t hear you.”

“Fuck me, ride my cock, let me come in your ass.” Sam flushed, an invisible force keeping him from looking away.

“That’s what I though you said.”

Sitting back on his legs, Gabriel finally stated moving, bouncing his body up and down Sams cock, still keeping Sam in the same position. Sam found himself watching his cock slipping in and out of him, how he moved with such ease, working Sam closer and closer to the edge. Sam gasped loudly as he got almost to the edge of orgasm and it was stopped right before he could actually go over it.

“Didn’t think it would be that easy, did you?” Gabe asked, wrapping his hand around his own cock, starting to stroke it in time with his hips.

“Please, please?”

“Soon enough, baby. Soon enough.”

Sam moaned again, still watching his cock, now with the view of Gabe stroking himself, the damp head moving in and out of the circle of his fist. He could tell that the angel was getting close, the pressure around his cock growing steadily tighter, Gabes moans starting to pick up, pleasure taking over smug on his face.

Just when Sam thought he would go crazy from not being able to come, Gabe finally fell over the edge, letting Sam come with him. When Sam was able to move again, he could barely register it, his limbs heavy now, Gabe propped up next to him, watching his breathing coming back. As he realized he could move, he wrapped his arm around Gabes waist, tilting his head up for a kiss.

“Feeling ok?” Gabriel asked, after a small kiss.

“Oh yeah.” Sam smiled, groaning as he moved his still back.

“How about a nice soak in a hot tub?” Gabe asked, brushing his finger tips over Sams collarbone.

“That sounds amazing.”


	7. Day Seven. Worship. Sastiel

**Summary for the Chapter:**

> Day Seven. Worship. Sastiel

**Notes for the Chapter:**

> Warnings: King of hell Sam

Cas supposed if he were human, the room would feel either chilly or overbearingly hot. While it was a wide open room, with just pillars, a red carpet, and the throne, it should in all logic be drafty. But since this particular throne room was also situated in Hell, that may not be the case at all, though since he was an angel, none of it mattered all that much; however it was something to think about when his king wasn’t around.

“Your Highness, please.” A voice from outside a set of side doors begged, but there wasn’t a response before the door opened and shut again.

Sam walked tall into the room, a dark look on his face as he came over and sat down heavily in his chair. Crawling over to Sam, Cas leaned over and kissed his feet, starting with the little toe and working across before working up to his ankles. He followed this path with both feet, before sitting up on his knees and resting his hands on Sams knees.

Though he didn’t say anything, Sam gave a small pet to Cas’s hair, leaning back again and shutting his eyes. Cas took that as his sign to keep going, pulling Sams lower clothes off and draping them over the arm on the throne. Going back to his ankles, he continued to kiss upwards, making sure to not leave a single place untouched. By the time Cas got to Sams cock, it was already hard and waiting for his mouth, and Cas was not one to disappoint.

Giving it the same treatment as the rest of him, he first worked it over with kisses, before working it with his tongue. Sam was panting lightly as Cas finally wrapped his lips around the head, sucking gently, then starting to move down. Without a gag reflex, Cas took his whole cock with no problem, lips pressed to the base, just letting Sam sit there for a moment.

Wrapping his fingers in Cas’s hair, he just held on as he started moving up and down, hollowing out his cheeks at each up movement. Sams breath was coming more labored as Cas continued to work him, hands resting on Sams thighs, thumbs rubbing circles on his balls. When Sam came it was sudden, would be over bearing for anyone else, but Cas swallowed with no problems, pulling back and licking his lips.

“Come here.” Sam said, using his king of Hell voice, that Cas wouldn’t refuse.

Climbing into his lap, Cas sat on his knees, hands resting, crossed, behind his back, waiting for whatever Sam wanted to do to him. The first touch to his cock made him jolt a little, but soon relaxed as Sam got to business. It didn’t take long for Cas to get close, worshiping his king always got him hot and bothered, but it wasn’t often that Sam would return the favor.

“Come for me.”

As Cas followed another order, Sam let him come all over his chest, some even getting on Sams chin and throat. When Cas came down from his high, he looked at the mess he made with wide eyes.

“I’ll clean you up.” He said, but was stopped as Sam shook his head.

“No, I have a meeting with some people that think I should get rid of you, if I’m not going to use your properly, this is my way of telling them to fuck off. Now be a good angel and get into place, our guests should be here soon.”

“Yes, Sir.”


	8. Day Eight. Role playing. Wincest

**Summary for the Chapter:**

> Day Eight. Role playing. Wincest

**Notes for the Chapter:**

> Warnings: None

Picking up his bottle, Sam took a long sip as he looked around the room, watching people dancing against each other. The music was just a bit too loud for his tastes, but it had a good beat that pulsed through you, making you feel it in your stomach. As the song changed, Sam finished off his beer, setting the bottle aside, trying to decide on another or just leaving. The choice was made for him as another was set down in front of him, a leather clad arm retracting once it was set down.

“Hey there sexy, looked like you needed another drink.”

Sam looked up at the man standing there, green eyes looking at him with something like hunger, making Sam swallow hard.

“Thank you?”

“Do you mind if I sit down, or are you waiting for someone?” He asked, finger spinning the bar stool top.

“You,” Sam cleared his throat. “You can sit down.”

The male smiled, making Sams heart flutter a little as he slid into the seat, knee pressing against Sams under the bar.

“What’s a little piece like you doing in a place like this?” He asked, looking at Sam with a smirk.

“Uhh. Just needed to get out of the house for a while.” Sam mumbled.

“Wife and kids keeping you down?”

“I’m not married. I live with my older brother.”

“Well that doesn’t sound very fun.” The mans eyes sparkled.

“It can be sometimes, though he’s kind of protected.” Sam shrugged.

“Huh. Bet you don’t get laid as much as you would like, with a brother like that. That’s why you’re really here isn’t it? Looking for someone to stick your dick in.”

“N-no.” Sam protested, his cheeks and neck turning red.

“Uh huh. Sure you’re not.” He winked, running his hand over Sams knee.

“Hey!” Sam said, pushing the males hand away.

“Now don’t be like that,” He smiled, putting his hand back. “I’m just here offering you what you really came here for. Even if you say it’s not. So I’ll be waiting in the alley right outside that door, and you come find me.”

The man gave his leg another squeeze before getting up and heading out said door, letting it close behind him. Sam watched the door for a few long moments before looking around, when he didn’t see anyone watching him, he got up and followed the green eyed man. Almost as soon as the door closed behind him, Sam found himself pressed against the wall.

“Told you so.” Was all he got before he was pulled into a kiss.

Sam groaned as the man pressed his hand over his crotch, massaging him almost too roughly, bringing his erection to life. The man continued to kiss him as he undid his belt and pants, pushing them down with no hesitation from Sam.

“Fuck.” Sam groaned, as the man sunk to his knees.

Wasting no time, the man got to work, sealing his mouth over Sams cock, holding his hips in place as he started to move. Somewhat Sam wished it could last longer, that there was more teasing, but they were in an alley way, that anyone could come out of the door at any second. And the man knew it too, as he took Sam as far as he could, working his tongue against the bottom and sides, sucking the head when it came to it. Sam tried to give a warning, but it happened so quickly that he didn’t have time, not that it seemed the male minded. When he finished swallowing the rest of Sams come, he pulled off with a small noise, before letting Sam pull his pants back up.

“Told you it would be hot.” Dean smiled, standing up.

“Yea, yea, shut up.” Sam huffed, shoving his shoulder. “Want me to take care of that?”

“Nah, you can just let me have that ass when we get back at the motel.”

Sam rolled his eyes, but nodded none the less. “Fine.”

“Then lets get out of here, shall we?”


	9. Day Nine. Frottage. Wincest

**Summary for the Chapter:**

> Day Nine. Frottage. Wincest

**Notes for the Chapter:**

> Warnings: None

The door was barely closed behind them when Dean pressed Sam against the wall, lips pressing hard against his. His hands were tangled in his hair, pulling the strands just enough to make the younger groan into his mouth. Knocking the back of Sams knee, made him bend just enough so their cocks could easily press together, through the thick fabric of their dress pants.

“Fuck, love when you play bad cop.” Dean moaned against his lips, pulling Sams other leg around his hip.

“Yea, this why you don’t let me more often?” Sam shot back, before his head fell back against the wall.

“Don’t get mouthy with me.” But there wasn’t a bite behind his words, pressing kisses against the front of Sams throat.

Sam could only moan as Dean continued to work their hips together, cocks slipping and sliding, rather than full on grinding, but neither could stop to move to the bed. Dean nipped at Sams neck now, chasing more moans, hands sliding down to hold Sams hips, pressing their hips harder together.

“Dean.” Sam gasped, fingers digging into Deans shoulders.

“That feel good, Sammy?”

“So good.”

“Does my baby boy want to come for me?”

“Fuck.”

Grabbing Sams ass, he pulled him as close as possible, pressing their lips together again, feeling his own orgasm getting close. Sam beat him by just seconds, wet spot forming on the dark fabric, Sams moans doing Dean in, letting him follow him over the edge. Sams leg slipped down, helping hold himself up as they tried to catch their breath.

“You know,” Sam panted. “Next time could you wait until we’re not wearing clothes, or at least ones that don’t need dry cleaning?”

“How are you even coherent right now?” Dean asked, giving him a bitch face, to which Sam just chuckled, kissing his nose just to see it deepen. “Stop that.”

“Never,”


	10. Day Ten. Gun play. Wincest

**Summary for the Chapter:**

> Day Ten. Gun Play. Wincest

**Notes for the Chapter:**

> Warnings: Uh. Gun

“Spread ‘um.”

Sam swallowed hard, shuffling his feet to the sides, a cold press of metal right below the back of his ear. A hand snapped out, patting Sam down quickly, lingering for a few long moments on Sams ass before moving again.

“Doesn’t feel like you’re carrying anything dangerous, besides that ass.”

Rolling his eyes, Sam turned his head to look at Dean, cocking an eyebrow.

“Really, that’s the best you got?”

“Shut your mouth boy.” Dean smirked, pulling the gun around and pressing it under Sams jaw.

With slow movements, Dean pulled Sam around so his back was now against the wall, the gun moving up and down each time Sam swallowed.

“Well well, looks like we’re going to have to find something to do with your mouth.”

There was a definite jump in Sams pants as he lowered himself to his knees, gun now pressed against the side of his neck. Dean lifted the hem of his shirt, motioning for Sam to do the rest, which he did, with shaky hands. Once the garments were down to Deans thighs, Dean wrapped his fingers in Sams locks, giving them a small squeeze, making Sams mouth pop open. Sam didn’t resist as Dean slid his cock in, groaning at the slick, warm slide.

“Damn, Sammy.” Dean huffed out, praise in his voice and smile.

Sam stayed still as Dean pulled back slowly, head nearly falling out of his mouth, before thrusting back in just as slow. Dean did this motion again, fingers now stroking Sams hair, but the gun never waivered against his neck, pressing in hard enough to bruise the delicate skin. On the fourth press did he finally start moving faster, moans falling from his lips as he used Sams mouth.

“Sammy, fuck.” He cursed, as the head of his cock pressed into Sams throat, Sam gasping softly.

The pitch of Deans moans changed as he got close, legs starting to shake as Sam continued to take what he was giving. His knees nearly gave out when he came, removing his hand from Sams hair, and holding himself up with the wall. Sam coughed a little when Dean pulled back, but nodded when Dean asked if he was ok.

“Do you want me to take care of that?” Dean motioning at Sams crotch, as he sunk to the floor with Sam.

“Nothing to take care of, just a shower and a new pair of boxers is in order.”

Dean chuckled, pressing his forehead against Sams shoulder, trying to get the feeling back in his legs, before taking care of his boy.


	11. Day Eleven. Orgasm denial. Wincest

**Summary for the Chapter:**

> Day Eleven. Orgasm denial. Wincest

**Notes for the Chapter:**

> Warnings: None

Sam was a moaning mess, fingers clutching at the pillows over his face, his bent legs shaking as Dean continued to press his fingers into him. Dean was sitting between his spread legs, one hand massaging his balls as the other worked, a smirk on his face.

“Dean, fuck.” Sam groaned.

“Uh uh. You made the joke, now your ass is cashing it in.”

Another groan slipped from his lips as he flashed back to what Dean was talking about, the joke he made to Cas. Not that Cas got it, when he said things were over in ten minutes flat most days, the angel just looked at him confused. Dean on the other hand, he got that look, the look that said Sam was in for a long night.

“That’s all it was, a joke!”

“Well, you do tell me I need to work on my sense of humor. So I’m not letting you come, at least not for a long while.”

“Ugh.”


	12. Day Twelve. Handjobs. Wincest

**Summary for the Chapter:**

> Day Twelve. Handjobs. Wincest

**Notes for the Chapter:**

> Warnings: None

The boys are tired, worn down and covered in bruises and cuts, standing in the shower is a pain in and of itself. By the time they actually fall into bed, Sam is half asleep, but at the same time he can feel the post hunt adrenaline coursing through him. And when Dean rolls against him, he can feel his hardness pressing against his thigh.

“Something you want?” Sam questions, around a yawn.

“Sleep?” Dean laughs, but it’s followed with a groan when Sam rubbed his leg against him.

“Nothing else?”

“Well, I won’t say no.”

Sam rolled his eyes, but moved onto his side, slipping his hand down Deans pants, wrapping his hand around him. Groaning, Dean shifted until he was able to do the same, resting his forehead to Sams, letting their moans mingle.

“Sammy.” Dean gasped, pressing their lips together, just enjoying what was happening, not pushing for it to end.


	13. Day Thirteen. Rimming. Wincest

**Summary for the Chapter:**

> Day Thirteen. Rimming. Wincest

**Notes for the Chapter:**

> Warnings: Short af. It's been a crazy few days

Dean groaned as Sam pressed his thighs, pushing him to be on his hands and knees, settling in behind him. Spreading his cheeks, Sam moved in, pressing his tongue against his hole, doing circles with his tongue. 

“Fuck, Sammy.” Dean groaned, as Sam pressed his tongue just slightly in, before going back to the circles.

“Feel good?” Sam asked, between licks.

Groaning again Dean pressed his face into his pillow, cock hard and leaking between his legs, letting Sam take care of him.


	14. Day Fourteen. Incest. Wincest

**Summary for the Chapter:**

> Day Fourteen. Incest. Wincest

**Notes for the Chapter:**

> Warnings: Incest play?

Sam cursed as Dean bent him over, two middle fingers pressing into his lubed hole, other hand holding in the middle of his back.

“Like that, don’t you, Sammy?”

“Fuck you.” Sam snapped, trying to hold in any noises.

“Oh, don’t you worry, little brother.”

“Don’t.” He whined, cock pulsing.

“Don’t? Don’t what,” Dean leaned closer, lips right by his ear. “Little brother.”

“You’re sick.”

Dean laughed, pressing a third finger into Sam, making him moan, head falling more, hair covering his face.

“I don’t think so, baby brother. I’m not the one getting off on your big brother fingering you.”

Sam whined, pressing back against Deans hand, urging him to move faster.

“Something you want, Sammy?”

“Please?” He breathed out.

“What was that?”

“Please.” Sam groaned louder.

“Please what? Use you’re big boy words.”

“Please fuck me, big brother!”

Now it was Deans turn to groan, his own cock starting to leak.

“Ok, baby boy, ok.”


	15. Day Fifteen. Lap dance. Wincest

**Summary for the Chapter:**

> Day Fifteen. Lap Dance. Wincest

**Notes for the Chapter:**

> Warnings: None

The alcohol was making Deans head fuzzy, his limbs feeling a little heavy and the music in the room flowing through him. Picking his glass up, he took another small drink, watching Sam in front of him, moving his hips. It wasn’t often that they played around like this, mostly they didn’t have the time, but Dean had declared a vacation. And a trip to a strip club had gotten Sam into this mood.

Walking closer, Sam ran his hands over Deans shoulders, leaning in and running the tip of his nose over Deans jaw. Straddling his legs, his hips were still moving slowly to the music, as he pulled his own shirt off, tossing it to the side.

“Am I going to get kicked out if I touch?” Dean asked, licking his bottom lip.

“I might kick you out if you don’t.” Sam smiled, putting Deans hands on his hips.


	16. Day Sixteen. Masks. Wincest

**Summary for the Chapter:**

> Day Sixteen. Masks. Wincest

**Notes for the Chapter:**

> Warnings: College era.

The room was over full of people, some getting way to close for Sams comfort as he tried to get to the drink table. He didn’t even want to be here, telling Dean that on the phone as he was getting ready, but Dean was right, he needed to have fun and just be a college kid. Didn’t stop him from wanting to run, especially since his height was pretty recognizable, even with the mask on his face. Finally getting to the table, he grabbed a beer and popped the top, before tossing it into the bowl for the lids. Taking a deep drink, he tried not to sigh, jumping a little when a hand grabbed his ass.

“Hey, do you.” Sam turned, his voice trailing off, looking into the green eyes behind the mask of the person who grabbed him.

“Sorry bout that.” He smirked, taking the beer from Sams lax hand, and taking a drink. “What’s a good looking guy like you doing all alone?”

“Thought my boyfriend was in another state.” Sam mumbled, unconsciously moving closer to him.

“Well then, I guess I can take you upstairs and have you all for myself. I’ll even keep the mask on.”

Sam licked his lips, standing for a few long moments, before he started following Dean towards the stairs, trying to ignore his suddenly aching cock.


End file.
